DE1932646C3 - l-Isoalkylamino-5-alkoxy- und 5-hydroxy-anthrachinone - Google Patents
l-Isoalkylamino-5-alkoxy- und 5-hydroxy-anthrachinoneInfo
- Publication number
- DE1932646C3 DE1932646C3 DE1932646A DE1932646A DE1932646C3 DE 1932646 C3 DE1932646 C3 DE 1932646C3 DE 1932646 A DE1932646 A DE 1932646A DE 1932646 A DE1932646 A DE 1932646A DE 1932646 C3 DE1932646 C3 DE 1932646C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- anthraquinone
- isopropylamino
- hydroxy
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000975 dye Substances 0.000 description 15
- 230000007935 neutral effect Effects 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- -1 alkyl radicals Chemical class 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VOACAQUGTUOOPB-UHFFFAOYSA-N 1-hydroxy-5-(propan-2-ylamino)anthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2NC(C)C VOACAQUGTUOOPB-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 235000011941 Tilia x europaea Nutrition 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000004571 lime Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLBXUJUVNQMHOQ-UHFFFAOYSA-N 1-methoxy-5-(propan-2-ylamino)anthracene-9,10-dione Chemical compound O=C1C2=C(NC(C)C)C=CC=C2C(=O)C2=C1C=CC=C2OC XLBXUJUVNQMHOQ-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- AFGMFDISBCNACC-UHFFFAOYSA-N [Na].O=C1C=2C(NC(C)C)=CC=CC=2C(=O)C2=C1C=CC=C2S(O)(=O)=O Chemical compound [Na].O=C1C=2C(NC(C)C)=CC=CC=2C(=O)C2=C1C=CC=C2S(O)(=O)=O AFGMFDISBCNACC-UHFFFAOYSA-N 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- DIPGQNOJYJXYKF-UHFFFAOYSA-N 1-amino-1-hydroxy-2H-anthracene-9,10-dione Chemical compound NC1(CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O)O DIPGQNOJYJXYKF-UHFFFAOYSA-N 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- URGUUPRXMYBPNE-UHFFFAOYSA-N 4-amino-5-hydroxy-1-(propan-2-ylamino)anthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C(N)=CC=C2NC(C)C URGUUPRXMYBPNE-UHFFFAOYSA-N 0.000 description 1
- REAMDQIWVXFRKG-UHFFFAOYSA-N 4-bromo-5-hydroxy-1-(propan-2-ylamino)anthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C(Br)=CC=C2NC(C)C REAMDQIWVXFRKG-UHFFFAOYSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- QYGWRTQROLYZPA-UHFFFAOYSA-N 9,10-dioxo-5-(propan-2-ylamino)anthracene-1-sulfonic acid Chemical compound O=C1C=2C(NC(C)C)=CC=CC=2C(=O)C2=C1C=CC=C2S(O)(=O)=O QYGWRTQROLYZPA-UHFFFAOYSA-N 0.000 description 1
- DHANLSHLIYXUPW-UHFFFAOYSA-N 9,10-dioxoanthracene-1,5-disulfonic acid;sodium Chemical compound [Na].O=C1C=2C(S(=O)(=O)O)=CC=CC=2C(=O)C2=C1C=CC=C2S(O)(=O)=O DHANLSHLIYXUPW-UHFFFAOYSA-N 0.000 description 1
- LIWRTTRIQSKPHK-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid;sodium Chemical compound [Na].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O LIWRTTRIQSKPHK-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/515—N-alkyl, N-aralkyl or N-cycloalkyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
- C09B1/06—Preparation from starting materials already containing the anthracene nucleus
- C09B1/14—Dyes containing ether groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1932646A DE1932646C3 (de) | 1969-06-27 | 1969-06-27 | l-Isoalkylamino-5-alkoxy- und 5-hydroxy-anthrachinone |
| DE19702013789 DE2013789A1 (de) | 1969-06-27 | 1970-03-23 | Verfahren zur Herstellung von l-Alkoxyanthrachinonen |
| DE19702013790 DE2013790A1 (de) | 1969-06-27 | 1970-03-23 | 1-Alkoxyanthrachinone |
| CH428373A CH544794A (de) | 1969-06-27 | 1970-06-08 | Verfahren zur Herstellung von 1-Alkoxy-anthrachinonen |
| CH857970A CH559228A5 (enrdf_load_stackoverflow) | 1969-06-27 | 1970-06-08 | |
| JP45054097A JPS4926289B1 (enrdf_load_stackoverflow) | 1969-06-27 | 1970-06-23 | |
| US49526A US3686232A (en) | 1969-06-27 | 1970-06-24 | Anthraquinones |
| NL7009383A NL7009383A (enrdf_load_stackoverflow) | 1969-06-27 | 1970-06-25 | |
| GB3087270A GB1311915A (en) | 1969-06-27 | 1970-06-25 | Anthraquinones and processes for their manufacture |
| BE752515D BE752515A (fr) | 1969-06-27 | 1970-06-25 | Anthraquinones et procede pour leur fabrication |
| FR7023755A FR2051373A5 (enrdf_load_stackoverflow) | 1969-06-27 | 1970-06-26 | |
| AT576570A AT299925B (de) | 1969-06-27 | 1970-06-26 | Verfahren zur Herstellung von neuen 1-Amino-anthrachinonen |
| AT430971A AT308086B (de) | 1969-06-27 | 1970-06-26 | Verfahren zur Herstellung von 1-Alkoxyanthrachinonen |
| AT430871A AT303713B (de) | 1969-06-27 | 1970-06-26 | Verfahren zur Herstellung von neuen 1-Alkoxyanthrachinonen |
| CA086,593A CA946383A (en) | 1969-06-27 | 1970-06-26 | Anthraquinones and processes for their manufacture |
| US05/279,756 US3971812A (en) | 1969-06-27 | 1972-08-11 | Anthraquinone dyestuffs |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1932646A DE1932646C3 (de) | 1969-06-27 | 1969-06-27 | l-Isoalkylamino-5-alkoxy- und 5-hydroxy-anthrachinone |
| DE19702013789 DE2013789A1 (de) | 1969-06-27 | 1970-03-23 | Verfahren zur Herstellung von l-Alkoxyanthrachinonen |
| DE19702013790 DE2013790A1 (de) | 1969-06-27 | 1970-03-23 | 1-Alkoxyanthrachinone |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1932646A1 DE1932646A1 (de) | 1971-04-08 |
| DE1932646B2 DE1932646B2 (de) | 1977-09-15 |
| DE1932646C3 true DE1932646C3 (de) | 1978-05-03 |
Family
ID=27182009
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1932646A Expired DE1932646C3 (de) | 1969-06-27 | 1969-06-27 | l-Isoalkylamino-5-alkoxy- und 5-hydroxy-anthrachinone |
| DE19702013789 Pending DE2013789A1 (de) | 1969-06-27 | 1970-03-23 | Verfahren zur Herstellung von l-Alkoxyanthrachinonen |
| DE19702013790 Pending DE2013790A1 (de) | 1969-06-27 | 1970-03-23 | 1-Alkoxyanthrachinone |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702013789 Pending DE2013789A1 (de) | 1969-06-27 | 1970-03-23 | Verfahren zur Herstellung von l-Alkoxyanthrachinonen |
| DE19702013790 Pending DE2013790A1 (de) | 1969-06-27 | 1970-03-23 | 1-Alkoxyanthrachinone |
Country Status (10)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3971812A (en) * | 1969-06-27 | 1976-07-27 | Bayer Aktiengesellschaft | Anthraquinone dyestuffs |
| US4166822A (en) * | 1971-11-22 | 1979-09-04 | Bayer Aktiengesellschaft | Branched-chain alkyl amino anthraquinones |
| DE2307591C3 (de) * | 1973-02-16 | 1982-05-13 | Bayer Ag, 5090 Leverkusen | Anthrachinonverbindungen, ihre Herstellung und ihre Verwendung |
-
1969
- 1969-06-27 DE DE1932646A patent/DE1932646C3/de not_active Expired
-
1970
- 1970-03-23 DE DE19702013789 patent/DE2013789A1/de active Pending
- 1970-03-23 DE DE19702013790 patent/DE2013790A1/de active Pending
- 1970-06-08 CH CH428373A patent/CH544794A/de not_active IP Right Cessation
- 1970-06-08 CH CH857970A patent/CH559228A5/xx not_active IP Right Cessation
- 1970-06-23 JP JP45054097A patent/JPS4926289B1/ja active Pending
- 1970-06-24 US US49526A patent/US3686232A/en not_active Expired - Lifetime
- 1970-06-25 NL NL7009383A patent/NL7009383A/xx unknown
- 1970-06-25 GB GB3087270A patent/GB1311915A/en not_active Expired
- 1970-06-25 BE BE752515D patent/BE752515A/xx unknown
- 1970-06-26 AT AT576570A patent/AT299925B/de not_active IP Right Cessation
- 1970-06-26 FR FR7023755A patent/FR2051373A5/fr not_active Expired
- 1970-06-26 AT AT430971A patent/AT308086B/de not_active IP Right Cessation
- 1970-06-26 AT AT430871A patent/AT303713B/de not_active IP Right Cessation
- 1970-06-26 CA CA086,593A patent/CA946383A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4926289B1 (enrdf_load_stackoverflow) | 1974-07-08 |
| US3686232A (en) | 1972-08-22 |
| BE752515A (fr) | 1970-12-01 |
| DE1932646A1 (de) | 1971-04-08 |
| DE2013789A1 (de) | 1971-10-21 |
| GB1311915A (en) | 1973-03-28 |
| AT299925B (de) | 1972-07-10 |
| FR2051373A5 (enrdf_load_stackoverflow) | 1971-04-02 |
| NL7009383A (enrdf_load_stackoverflow) | 1970-12-29 |
| DE1932646B2 (de) | 1977-09-15 |
| CH559228A5 (enrdf_load_stackoverflow) | 1975-02-28 |
| CA946383A (en) | 1974-04-30 |
| AT303713B (de) | 1972-12-11 |
| DE2013790A1 (de) | 1971-10-14 |
| CH544794A (de) | 1974-01-15 |
| AT308086B (de) | 1973-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |